The Comedy of Creepiness: An Unsettling, Yet Smooth Jazz-Rock Fable About a Deadbeat Who Wants to Woo His Own Relatives.
For those of us who came of age with the meticulously polished cynicism of Steely Dan, the year 2000 reunion album, Two Against Nature, felt less like a comeback and more like a mysterious, perfectly preserved artifact unearthed from the 1970s. And nestled among its tracks was “Cousin Dupree,” a song that managed to be simultaneously lighthearted and deeply unsettling, proving that Donald Fagen and Walter Becker had not lost their perverse, razor-sharp edge. It is a masterpiece of musical misdirection, where a bouncy, immaculate jazz-rock groove soundtracks a narrative of profound awkwardness and familial impropriety.
Key Information: “Cousin Dupree” was released in 2000 as a promotional single from Steely Dan’s eighth studio album, Two Against Nature. The song did not chart on the Billboard Hot 100 but garnered significant industry recognition, winning the prestigious Grammy Award for Best Pop Performance by a Duo or Group with Vocal in 2001. This single’s success was a major factor in the album’s dramatic sweep at the 43rd Annual Grammy Awards, where Two Against Nature controversially took home the coveted Album of the Year award, beating out releases by younger acts like Radiohead and Eminem. The album itself was a commercial success, peaking at No. 6 on the US Billboard 200 chart.
The story behind “Cousin Dupree,” like so much of the Steely Dan catalogue, is rooted in the seedy underbelly of Americana, viewed through a lens of high musical sophistication. The song details the exploits of the titular Cousin Dupree, an aging, broke, and pathetically hopeful layabout who shows up unannounced at his relatives’ home, fully expecting to charm his way into their good graces—and, more disturbingly, into the bed of his attractive younger cousin, Janine. The drama is played out entirely in the narrator’s self-deluded monologue. He is a loser with a silver tongue, a classic Steely Dan archetype: the morally dubious character convinced of his own charm despite overwhelming evidence to the contrary.
Donald Fagen and Walter Becker themselves offered cryptic, deadpan insights into the character, suggesting the song had a “rural narrative” fitting into the “folk humour tradition” of inbred families, although Becker quickly and typically broadened the scope, noting that “Cousin Duprees in all kinds of families.” The song’s darkness—the underlying themes of sexual opportunism and familial parasitism—is made palatable, even seductive, by the music. The track features the kind of airtight, funky groove that could only be achieved by the highest-caliber session players, including the effortless drumming of Leroy Clouden and the slick, perfectly placed guitar solos delivered by Walter Becker himself. The contrast between the moral decay in the lyrics and the sonic perfection is the essence of the Steely Dan dramatic style.
The profound meaning of “Cousin Dupree” is not merely in its creepy premise, but in its masterful portrayal of denial and self-absorption. The lyrics are delivered from Dupree’s perspective, allowing us to eavesdrop on his delusional inner world: “I’ve been down, but I’m ready to soar / Got a little sweet surprise for my sweet Janine.” He dismisses her skepticism—her observation that he has a “skeevey look” and the “dreary architecture of [his] soul”—with the casual, misplaced confidence of a man incapable of seeing his own reflection. For the older, well-informed listener who remembers the band’s initial run, “Cousin Dupree” was a deeply nostalgic experience. It confirmed that the intellectual rock drama of Steely Dan—their commitment to technical brilliance and lyrical malice—had survived the decades completely intact, a glorious, albeit morally compromised, triumph of art over time.